EP0688761A2 - L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses - Google Patents

L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses Download PDF

Info

Publication number: EP0688761A2
Authority: EP; European Patent Office
Prior art keywords: composition; cosmetic; treating; pharmaceutical compositions; carnitine
Prior art date: 1994-06-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP95830209A

Other languages

German (de)

English (en)

French (fr)

Other versions

EP0688761A3 (es

Inventor

Claudio Cavazza

Paolo Cavazza

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Avantgarde SpA

Original Assignee

Avantgarde SpA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-06-20

Filing date

1995-05-18

Publication date

1995-12-27

1995-05-18 Application filed by Avantgarde SpA filed Critical Avantgarde SpA

1995-12-27 Publication of EP0688761A2 publication Critical patent/EP0688761A2/en

1996-01-17 Publication of EP0688761A3 publication Critical patent/EP0688761A3/xx

Status Withdrawn legal-status Critical Current

Links

208000017520 skin disease Diseases 0.000 title claims abstract description 8
239000002537 cosmetic Substances 0.000 title claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title description 5
CGALRBHTEZSWGM-SSDOTTSWSA-N (3r)-3-(2-hydroxyacetyl)oxy-4-(trimethylazaniumyl)butanoate Chemical compound C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CO CGALRBHTEZSWGM-SSDOTTSWSA-N 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 17
239000002674 ointment Substances 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 8
208000001840 Dandruff Diseases 0.000 claims description 6
208000013270 Palmar hyperkeratosis Diseases 0.000 claims description 5
208000014417 Plantar hyperkeratosis Diseases 0.000 claims description 5
239000006071 cream Substances 0.000 claims description 4
208000002874 Acne Vulgaris Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
206010000496 acne Diseases 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
230000003780 keratinization Effects 0.000 claims description 3
239000006210 lotion Substances 0.000 claims description 3
239000000243 solution Substances 0.000 claims description 3
230000002950 deficient Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
238000011282 treatment Methods 0.000 description 12
206010021198 ichthyosis Diseases 0.000 description 11
210000003491 skin Anatomy 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 6
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000003902 lesion Effects 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
229960004889 salicylic acid Drugs 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 2
208000001913 Lamellar ichthyosis Diseases 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
201000000751 autosomal recessive congenital ichthyosis Diseases 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000008311 hydrophilic ointment Substances 0.000 description 2
239000002085 irritant Substances 0.000 description 2
231100000021 irritant Toxicity 0.000 description 2
229940066842 petrolatum Drugs 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229930002330 retinoic acid Natural products 0.000 description 2
210000004761 scalp Anatomy 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
229960001727 tretinoin Drugs 0.000 description 2
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
206010010356 Congenital anomaly Diseases 0.000 description 1
206010048768 Dermatosis Diseases 0.000 description 1
208000028782 Hereditary disease Diseases 0.000 description 1
206010020649 Hyperkeratosis Diseases 0.000 description 1
206010021197 Ichthyoses Diseases 0.000 description 1
208000026350 Inborn Genetic disease Diseases 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
208000024556 Mendelian disease Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
208000001001 X-linked ichthyosis Diseases 0.000 description 1
206010048218 Xeroderma Diseases 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000008294 cold cream Substances 0.000 description 1
229940124448 dermatologic drug Drugs 0.000 description 1
239000003599 detergent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000002962 histologic effect Effects 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
208000003532 hypothyroidism Diseases 0.000 description 1
230000002989 hypothyroidism Effects 0.000 description 1
201000002597 ichthyosis vulgaris Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011221 initial treatment Methods 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000003410 keratolytic agent Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
238000000034 method Methods 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000037311 normal skin Effects 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
208000012111 paraneoplastic syndrome Diseases 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical group CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms

Definitions

the present invention relates to a novel L-carnitine salt and the use thereof for producing cosmetic and pharmaceutical compositions which contain such salt, suitable to be topically applied for the treatment of dermatoses.
This novel L-carnitine salt is L-carnitine glycolate of formula (I)
L-carnitine glycolate is a highly stable and non-hygroscopic salt. This is quite surprising since glycolic acid is somewhat hygroscopic. Surprising as well is the activity of this novel salt as dermatologic drug if one considers that glycolic acid is mildly irritant to skin and mucous membranes.
L-carnitine inner salt (16.1 g; 0.1 moles) was dissolved in 100 mL H2O.
Glycolic acid (7.6 g; 0.1 moles) was added to the solution.
L-carnitine glycolate is used as active ingredient for producing dermatologic and cosmetic compositions suitable to be topically applied.
the dermatoses which are suitably treated with the compositions of the present invention are in particular ichthyosis, psoriasis and those dermatoses which are induced by a defective keratinization, such as dandruff, acne and palmar and plantar hyperkeratosis.
Ichthyosis is a dermatosis characterized by generalized dryness, harshness and scaling of the skin. It may occur as a hereditary disease present at birth, or as a metabolic disorder associated with hypothyroidism or with the intake of drugs (such as butyrophenols) inhibiting lipid synthesis, or as a paraneoplastic syndrome, manifestation of a tumor process involving internal organs.
drugs such as butyrophenols
Xeroderma the mildest form of ichthyosis is neither congenital nor associated with systemic abnormalities.
the inherited ichthyoses all characterized by excessive accumulation of scale on the skin surface, are classified according to clinical, genetic, and histologic criteria.
Known treatments of any form of ichthyosis comprise topically applying to the skin hydrating emollients. Furthermore, salicylic acid or vitamin A-containing ointments have been widely used.
a keratolytic agent particularly effective in removing the scales in ichthyosis vulgaris, lamellar ichthyosis and sex-linked ichthyosis contains 6% salicylic acid in a gel composed of propylene glycol, ethanol, hydroxypropylene cellulose and water.
drugs for the treatment of this disorder include: 50% propylene glycol in water, hydrophilic petrolatum and water (in equal parts), and cold cream.
tretinoin vitamin A acid: retinoic acid
Hyperkeratosis is a thickening of the stratum corneum of the skin.
the treatment of choice is the topical application of drugs containing urea, propylene glycol or salicylic acid. Also in this case, none of the known treatment has proved to be satisfactorily effective.
the compound of the present invention when topically applied as solutions, lotions, creams or ointments containing from 0.01% to 20%, preferably from 1% to 15% and most preferably from 2 to 10% by weight of the compound, is potently effective in achieving complete remission of ichthyotic conditions in humans and in healing psoriasis and those disorders brought about by an altered keratinization, such as dandruff, acne and palmar and plantar hyperkeratosis.
L-carnitine glycolate is first preferably dissolved in water or ethanol.
the solution thus prepared may be admixed in the conventional manner with commonly available ointment bases such as hydrophilic ointments (USP) or petrolatum (USP).
USP hydrophilic ointments
USP petrolatum
the water or ethanol used to dissolve the compound of this invention may range in concentration of from 1 to 30%, by volume, of the total composition.
the compound of this invention may also be formulated in a solution or lotion form.
the salt is dissolved directly in a mixture of water, ethanol and propylene glycol (40:40:20 by weight).

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Birds (AREA)
Dermatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Zoology (AREA)
Nutrition Science (AREA)
Physiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)

EP95830209A 1994-06-20 1995-05-18 L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses Withdrawn EP0688761A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITRM940396A IT1272290B (it)	1994-06-20	1994-06-20	Sale della l-carnitina e composizioni farmaceutiche che lo contengono per il trattamento di affezioni cutanee
ITRM940396		1994-06-20

Publications (2)

Publication Number	Publication Date
EP0688761A2 true EP0688761A2 (en)	1995-12-27
EP0688761A3 EP0688761A3 (es)	1996-01-17

Family

ID=11402602

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
EP95830209A Withdrawn EP0688761A2 (en)	1994-06-20	1995-05-18	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
EP95109027A Expired - Lifetime EP0697397B1 (en)	1994-06-20	1995-06-12	L-carnitine salt and compositions containing same

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
EP95109027A Expired - Lifetime EP0697397B1 (en)	1994-06-20	1995-06-12	L-carnitine salt and compositions containing same

Country Status (13)

Country	Link
US (1)	US5591450A (es)
EP (2)	EP0688761A2 (es)
JP (2)	JPH0827081A (es)
KR (2)	KR960000855A (es)
AT (1)	ATE165338T1 (es)
CA (2)	CA2150407A1 (es)
DE (1)	DE69502147T2 (es)
ES (1)	ES2116651T3 (es)
HK (1)	HK1004918A1 (es)
IT (1)	IT1272290B (es)
PH (1)	PH31606A (es)
TW (1)	TW300881B (es)
ZA (2)	ZA955024B (es)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0697397B1 (en) *	1994-06-20	1998-04-22	AVANTGARDE S.p.A.	L-carnitine salt and compositions containing same
WO2003000700A3 (en) *	2001-06-25	2004-11-18	Biosalts Srl	Ascorbyl derivatives of carnitines and cosmetic compositions containing same
EP1610760A4 (en) *	2003-03-28	2008-01-09	Lonza Ag	TOPICAL COMPOSITIONS OF L-CARNITINE

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AUPN115095A0 (en) *	1995-02-15	1995-03-09	Butt, Henry Lawrence	Analysis of and compositions and methods for the treatment of disease
IT1276253B1 (it)	1995-12-15	1997-10-27	Sigma Tau Ind Farmaceuti	Composizione farmaceutica contenente l-carnitina o alcanoil l-carnitine per la prevenzione ed il trattamento di stati morbosi
IT1289974B1 (it) *	1997-02-25	1998-10-19	Aldo Fassi	Procedimento per la produzione di sali stabili e non igroscopici di l(-)carnitina e di alcanoli l(-)-carnitine
IT1291113B1 (it) *	1997-03-20	1998-12-29	Sigma Tau Ind Farmaceuti	Composizione nutritiva terapeutica per soggetti affetti da diabete mellito
US6080788A (en) *	1997-03-27	2000-06-27	Sole; Michael J.	Composition for improvement of cellular nutrition and mitochondrial energetics
US5863940A (en)	1997-12-01	1999-01-26	Sigma-Tau Healthscience S.P.A.	Medicament and therapeutical method for treating idiopathic asthenozoospermia
US6090848A (en) *	1997-12-01	2000-07-18	Sigma-Tau Healthscience S.P.A.	Compositions and methods for increasing the concentration and/or motility of spermatozoa in humans
DK0951909T4 (da)	1998-03-19	2011-01-24	Sigma Tau Ind Farmaceuti	Kombinationspræparat omfattende en L-carnitin eller en alkanoyl-L-carnitin, en glycosaminoglycan og/eller bestanddel deraf
KR20000050756A (ko) *	1999-01-14	2000-08-05	연규	핀 귀걸이의 제조방법과 그 제품의 구조
US6090849A (en) *	1999-03-23	2000-07-18	The Board Of Regents For Oklahoma State University	Carnitine supplemented diet to prevent sudden death syndrome in breeder type poultry
JP4539096B2 (ja) *	2004-01-16	2010-09-08	日油株式会社	油性成分被覆ｌ−カルニチン塩粉末およびその用途
CN1322860C (zh) *	2004-08-31	2007-06-27	北京正大绿洲医药科技有限公司	左旋肉碱滴丸及其制备方法
US7572832B2 (en) *	2007-03-19	2009-08-11	Biolink Life Sciences, Inc.	Non-hygroscopic L-carnitine salts
KR101633846B1 (ko)	2013-11-25	2016-06-27	주식회사 엘지화학	도전성 패턴 형성용 조성물 및 도전성 패턴을 갖는 수지 구조체
US10118911B2 (en) *	2015-03-27	2018-11-06	Jiangsu Hengrui Medicine Co., Ltd.	P-toluenesulfonate for MEK kinase inhibitor, and crystal form thereof and preparation method therefor
CN107216339B (zh) *	2016-03-22	2021-05-04	中国科学院上海药物研究所	一种dppiv抑制剂马来酸盐的多晶型及其制备方法
CN107216340B (zh) *	2016-03-22	2021-05-04	中国科学院上海药物研究所	一种dppiv抑制剂的盐型及其制备方法
SE542106C2 (en) *	2016-08-26	2020-02-25	Atif M Dabdoub	Dietary macro/micronutritional supplement for patients undergoing kidney dialysis

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EP0150688B1 (en)	1983-12-28	1987-04-22	Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.	Salts of l-carnitine and alkanoyl l-carnitines and process for preparing same
FR2627385B3 (fr) *	1988-02-23	1991-08-23	Serobiologiques Lab Sa	Composition notamment utile comme matiere de base pour la preparation de compositions pharmaceutiques, notamment dermatologiques et/ou cosmetiques
US4968719A (en) *	1989-04-03	1990-11-06	Sigma Tau, Industrie Farmaceutiche Riunite Spa	Method for treating vascular disease
US5137910A (en) *	1989-05-05	1992-08-11	C.D. Searle & Co.	Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders
IT1263013B (it) *	1992-10-20	1996-07-23	Avantgarde Spa	Esteri della l-carnitina e di alcanoil l-carnitine con l'acido glicolico o suoi esteri e composizioni farmaceutiche contenenti tali per il trattamento di affezioni cutanee.
IT1261984B (it) *	1993-06-22	1996-06-11	Avantgarde Spa	Uso di esteri della l-carnitina o di acil l- carnitine con idrossiacidi per produrre composizioni farmaceutiche per il trattamento di affezioni cutanee.
IT1272290B (it) *	1994-06-20	1997-06-16	Avantgarde Spa	Sale della l-carnitina e composizioni farmaceutiche che lo contengono per il trattamento di affezioni cutanee

1994
- 1994-06-20 IT ITRM940396A patent/IT1272290B/it active IP Right Grant
1995
- 1995-05-18 EP EP95830209A patent/EP0688761A2/en not_active Withdrawn
- 1995-05-29 CA CA002150407A patent/CA2150407A1/en not_active Abandoned
- 1995-06-02 KR KR1019950014607A patent/KR960000855A/ko not_active Withdrawn
- 1995-06-07 US US08/473,208 patent/US5591450A/en not_active Expired - Fee Related
- 1995-06-12 ES ES95109027T patent/ES2116651T3/es not_active Expired - Lifetime
- 1995-06-12 DE DE69502147T patent/DE69502147T2/de not_active Expired - Fee Related
- 1995-06-12 EP EP95109027A patent/EP0697397B1/en not_active Expired - Lifetime
- 1995-06-12 AT AT95109027T patent/ATE165338T1/de not_active IP Right Cessation
- 1995-06-13 PH PH50702A patent/PH31606A/en unknown
- 1995-06-16 KR KR1019950015962A patent/KR960000217A/ko not_active Withdrawn
- 1995-06-16 CA CA002152005A patent/CA2152005A1/en not_active Abandoned
- 1995-06-19 ZA ZA955024A patent/ZA955024B/xx unknown
- 1995-06-19 JP JP7151457A patent/JPH0827081A/ja active Pending
- 1995-06-19 ZA ZA955025A patent/ZA955025B/xx unknown
- 1995-06-20 JP JP7153148A patent/JPH0826984A/ja active Pending
- 1995-06-20 TW TW084106325A patent/TW300881B/zh active
1998
- 1998-05-09 HK HK98104024A patent/HK1004918A1/en not_active IP Right Cessation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0697397B1 (en) *	1994-06-20	1998-04-22	AVANTGARDE S.p.A.	L-carnitine salt and compositions containing same
WO2003000700A3 (en) *	2001-06-25	2004-11-18	Biosalts Srl	Ascorbyl derivatives of carnitines and cosmetic compositions containing same
EP1610760A4 (en) *	2003-03-28	2008-01-09	Lonza Ag	TOPICAL COMPOSITIONS OF L-CARNITINE

Also Published As

Publication number	Publication date
ZA955024B (en)	1996-02-08
KR960000855A (ko)	1996-01-25
JPH0827081A (ja)	1996-01-30
JPH0826984A (ja)	1996-01-30
ES2116651T3 (es)	1998-07-16
EP0697397B1 (en)	1998-04-22
ITRM940396A0 (it)	1994-06-20
CA2150407A1 (en)	1995-12-21
IT1272290B (it)	1997-06-16
EP0688761A3 (es)	1996-01-17
EP0697397A1 (en)	1996-02-21
HK1004918A1 (en)	1998-12-11
US5591450A (en)	1997-01-07
ITRM940396A1 (it)	1995-12-20
ZA955025B (en)	1996-02-08
DE69502147T2 (de)	1998-08-13
ATE165338T1 (de)	1998-05-15
DE69502147D1 (de)	1998-05-28
KR960000217A (ko)	1996-01-25
TW300881B (es)	1997-03-21
PH31606A (en)	1998-11-03
CA2152005A1 (en)	1995-12-21

Legal Events

Date	Code	Title	Description
1995-11-10	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1995-11-29	PUAL	Search report despatched	Free format text: ORIGINAL CODE: 0009013
1995-12-27	AK	Designated contracting states	Kind code of ref document: A2 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE
1996-01-17	AK	Designated contracting states	Kind code of ref document: A3 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE
1996-05-08	17P	Request for examination filed	Effective date: 19960220
1997-03-26	17Q	First examination report despatched	Effective date: 19970204
1997-10-31	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
1997-12-17	18D	Application deemed to be withdrawn	Effective date: 19970617

Publication	Publication Date	Title
EP0688761A2 (en)	1995-12-27	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
EP0700898B1 (en)	1997-11-26	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
US3920835A (en)	1975-11-18	Treatment of disturbed keratinization
US3988470A (en)	1976-10-26	Treatment of palmar and plant disturbed keratosis
EP0628309B1 (en)	1999-03-24	Use of O-esters of L-carnitine for the treatment of dermatoses
EP0596838B1 (en)	1996-05-29	Esters of L-carnitine and alkanoyl L-carnitines with glycolic acid or esters thereof and pharmaceutical compositions containing same for treating dermatoses
EP0631779B1 (en)	1997-08-20	Use of esters of L-carnitine and acyl L-carnitine with hydroxyacids for producing pharmaceutical compositions for treating dermatoses
HK1005589B (en)	1999-01-15	Esters of l-carnitine and alkanoyl l-carnitines with glycolic acid or esters thereof and pharmaceutical compositions containing same for treating dermatoses
EP0578077A2 (en)	1994-01-12	Compositions containing retinoic acids and tocopherol
US5639767A (en)	1997-06-17	Therapeutical method for treating dermatoses based on the use of O-esters of L-carnitine with aromatic acids
EP0700897B1 (en)	1998-07-29	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
US4021573A (en)	1977-05-03	Psoriasis treatment with retinoic acid analogs
HK1009961A (en)	1999-06-11	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
HK1004917B (en)	1998-12-11	L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses
HK1008660A (en)	1999-05-14	Use of esters of l-carnitine and acyl l-carnitine with hydroxyacids for producing pharmaceutical compositions for treating dermatoses.

EP0688761A2 - L-carnitine salt and cosmetic and pharmaceutical compositions containing same for treating dermatoses - Google Patents

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